Hydrochloric Acid → 5-Cyano-2-methoxybenzoic acid
Reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:13][CH3:14])=[C:7]([CH:12]=1)[C:8]([O:10]C)=[O:9])#[N:2].[OH-].[Na+].Cl>O1CCOCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:13][CH3:14])=[C:7]([CH:12]=1)[C:8]([OH:10])=[O:9])#[N:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Methyl 5-cyano-2-methoxybenzoate (2 g) obtained in step A of Example 1-3-1 was dissolved in 28 mL of 1,4-dioxane, and 21 mL of an aqueous solution of 2.5 mols of sodium hydroxide was added. After stirring for 30 minutes at room temperature, the reaction mixture was cooled in an ice bath, and neutralized with the use of 50 mL of 1 M hydrochloric acid. The resulting aqueous solution was extracted 6 times with methylene chloride. The respective organic layers were combined, whereafter the combined organic layer was washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The anhydrous sodium sulfate was separated by filtration, and washed with methylene chloride. The filtrate and the washings were combined, and methylene chloride was distilled off under reduced pressure. The resulting solid was dried under reduced pressure to obtain 1.6 g (87%) of 5-cyano-2-methoxybenzoic acid.
Workup
- temperaturethe reaction mixture was cooled in an ice bath
- extractionThe resulting aqueous solution was extracted 6 times with methylene chloride
- washwas washed with a saturated aqueous solution of sodium chloride
- dry with materialdried over anhydrous sodium sulfate
- customThe anhydrous sodium sulfate was separated by filtration
- washwashed with methylene chloride
- distillationmethylene chloride was distilled off under reduced pressure
- customThe resulting solid was dried under reduced pressure
Sources & evidence
- ORD record
- ord-a4763a5705f340fb8fcd121a9b306c53
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063046B2
Reaction notes
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